Triethylamine → 1-(3,3-Dimethylcyclobutyl)-3-(2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea

HRID 522709Notes

Reaction equation

HRID 522709 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:5][CH:4](C(O)=O)[CH2:3]1.[F:10][C:11]1[CH:17]=[C:16]([CH3:18])[C:15]([B:19]2[O:23][C:22]([CH3:25])([CH3:24])[C:21]([CH3:27])([CH3:26])[O:20]2)=[CH:14][C:12]=1[NH2:13].C([N:30]([CH2:33]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:42])C=CC=CC=1>O1CCOCC1>[CH3:9][C:2]1([CH3:1])[CH2:3][CH:4]([NH:30][C:33]([NH:13][C:12]2[CH:14]=[C:15]([B:19]3[O:23][C:22]([CH3:25])([CH3:24])[C:21]([CH3:27])([CH3:26])[O:20]3)[C:16]([CH3:18])=[CH:17][C:11]=2[F:10])=[O:42])[CH2:5]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2151063,3-Dimethylcyclobutanecarboxylic acidHCID 690365482-Fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 1236543741-(3,3-Dimethylcyclobutyl)-3-(2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureaYield 49%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Heat a mixture of 3,3-dimethylcyclobutanecarboxylic acid (0.230 g, 1.792 mmol), 2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.30 g, 1.195 mmol), triethylamine (TEA) (0.331 mL, 2.389 mmol) and diphenylphosphoryl azide (DPPA) (0.519 mL, 2.389 mmol) in dioxane (10 mL) at 100° C. for 2 h. Cool the mixture to RT, concentrate to dryness and purify via silica gel chromatography (10-100% EtOAc/Hexanes) to afford the title compound (220 mg, 49% yield). MS (m/z): 377.2 (M+1).

Workup

  1. temperatureHeat
  2. concentrationconcentrate to dryness
  3. custompurify via silica gel chromatography (10-100% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-2752525185934e43aa5043b5481f4608
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Reaction notes

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